Process for making n-(1, 1-dimethyl-3-hydroxybutyl)-lactamide



Patented Jan. 5, 1954 PROCESS FOR MAKING N- (1,1-DIMETHYL-3- HY DROXYBUTYL) -LACTAMIDE William P. Ratchford, Philadelphia,

Pa., assignor to the United States of America as represented by the Secretary of Agriculture N Drawing.

1951, Serial Original application March 23, No. 217,281, now Patent No.

2,648,664, dated August 11, 1953. Divided and this application March 26, 1953, Serial No.

1 Claim.

(Granted under Title 35, U. S. Code (1952),

sec. 266) I have found that this compound can be obtained by forming a mixture of methyl ethyl or propyl lactate with about an equimolecular amount, pref erably a slight excess, of 2-amino-2-methylpenta noll, and maintaining the resulting solution at room temperature (about 25 (3.), for example, until the reaction has proceeded substantially to completion, which is usually attained within a few days. The reaction product is then recovered by distillation.

The oxazine is a basic compound with an alcod holic hydroxyl group. Hence the latter group can be acylated, as by a long-chain aliphatic carboxylic acid; the salts of this ester should be water-soluble to give soapy solutions with wetting-out, emulsifying and dispersing properties. Similar compounds have been disclosed by Jayne and Day, U. S. 2,329,619, September 14, 19 13.

Moreover the oxazine is readily hydrolyzed by an equimolecular amount of water to give N-(1,1- dimethyl-3-hydroxybutyl) -lactarnide:

I+H20=CH3 CHOHCONHC CH3) zCHzCHOHCHs Thus the oxazine is also a valuable intermediate for purification of N-(1,1-dimethyl-3-hydroxybutyl) -1actamide.

The latter, having two hydroxyl groups, may be considered a glycol. As such, it may be acylated. to give esters which plasticize cellulose resins and synthetic resins of the polyvinyl chloride-acetate type. Such esters are the diacetate, which plasticizes cellulose acetate; the dipropionate, which plasticizes cellulose acetate and ethyl cellulose; and the di-2-ethylhexanoate, which plasticizes ethyl cellulose and polyvinyl chloride-acetate.

The lactamide can also be reacted with polycarboxylic acids to make alkyd resins.

Thus, aside from its own usefulness, the oxazine aiiords a means for transporting the valuable lactamide in a concentrated and liquid form. The oxazine is equivalent to about 110 percent of the lactamide.

The following example illustrates the invention:

A mixture consisting of 104 g. methyl lactate and. 128 g. of 2-amino-2-methy1pentanol-4, was allowed to stand at room temperature for 7 days. At the end of this period the extent of aminolysis was 97 percent as determined by titration of a sample of the reaction mixture with 0.1 N hydrochloric acid to the grey transition point of a mixed indicator consisting of 4 parts 0.1 percent methyl red and 1 part 0.1 percent methylene blue in 95 percent alcohol. The reaction mixture was then distilled first at atmospheric pressure to remove a methanol fraction, and then under reduced pressure to remove water. The 4,4,6-trimethyl 2 (1 hydroxyethyl) 5,6 dihyclro- 1,3,4H-oxazine was next collected at 95-105" (3/ 30 mm., as a mobile colorless liquid, neutralization equivalent 171. The yield was percent of the theoretical. The product so obtained on being combined with an equimolecular amount of Water at room temperature is quantitatively converted to N-1,1-dimethyl-3-hydroxybutyllactamide, M. P. 94-94.5 C.

, If preferred, the oxazine need not be isolated from the reaction mixture. After removal of methanol and water, the residual oxazine may be stored, then the lactamide obtained subsequently by addition of water.

The oxazine may also be designated 4,4,6-tri- 3 methyl 2 (1 hydroxyethyl) 5,6 dihydro- 1,3,4-oxazine.

Having thus described my invention, I claim: The process of producing N-(1,1-dimethy1-3- hydroxybutyl) -1actamide by reacting a compound having the formula:

cmcnon-c c xcnm with an equimoleeular amount of water at room temperature.

WILLIAM F. RATCHFORD.

Ratchford, Ind. and Eng. Chem.," 

